We swoop around another turn in the mountains. the road gets a bit steeper, and in the January rain, a gray tendril of mist drifts over the green woods. The engine churns as our car labors uphill. beside me, the little boy in a car seat stares out the window. Christian Thomas is five years old and reed-thin with rosy, cherubic cheeks, and by now he has eaten about half of the chocolate donut holes contained in the 14-ounce Walmart box in his lap. What’s on his mind? Is he dreading the hike planned for today? Plenty of adults would be anxious about a 15-mile trek in a chilly downpour, hoofing it up and down on the Appalachian Trail as it rolls through Shenandoah National Park. Or is he just mesmerized by the fat raindrops lashing at the windows?

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Quiet, quiet, quiet. There are crinkled paper bags wadded on the floor of the car, a thrashed 1996 Jeep Cherokee, and dirty laundry is strewn everywhere. Yet somehow amid the chaos, this kid is tranquil, composed—put together. His brown hair is neatly parted. His manner is genial, and when he speaks he exudes the incongruous panache of a TV reporter delivering the news from outside a low-rent apartment complex. “I like fog,” he says in a high, fluty voice. “It’s cool! When you see a person, it’s like, wow, he magicked here.”

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Christian giggles, charmed by his own wit. Then he keeps eating donut holes and his mother turns around to peer back at him. Andrea Rego is 26, with long brunette pigtails. In her most recent job, she did office work at a construction company on Long Island. She can be feisty. Like a moment ago, frustrated, she said, “I’m gonna burn this car when this trip is done!” Now, in a sweet baby voice, she tells her son, “You can have as many of those as you want, bud. Eat up.” She turns to me and adds, “I’d be happy if he ate the whole box. He needs the calories.”

Maybe he does: It’s early 2014 and Christian is hiking the entire Appalachian Trail, all 2,180 miles, with his mom and stepdad (well, technically his mom’s boyfriend), Dion Pagonis, 29. Christian—now best known by his trail name, Buddy Backpacker—started eight months ago, in Harper’s Ferry, West Virginia, and he’s trudged through snow in North Carolina and black flies in Maine. He’s slept with his Pooh Bear every night and he’s out-hiked his mom. She stopped after just 400 miles, electing to chauffeur, which improved their resupply logistics and enabled Buddy and Dion to walk without heavy packs. In a week, after hiking numerous trail sections out of sequence, the trio will return to Harper’s Ferry. Christian will become the youngest person in history to complete the AT. After that, the family plans to hike the Pacific Crest Trail (2,650 miles) and the Continental Divide Trail (3,100 miles).

At the moment, Christian weighs just 46 pounds. So he keeps eating donut holes, and then, after a while, he groans. “I don’t feel too good, Mommy,” he says. “My stomach hurts.”

We park at the trailhead, and when we climb out of the car the wind is ripping. When Andrea pulls a transparent rain poncho over Christian’s jacket, it rattles in the gale. No other hikers are out. There are hardly any cars in the whole park, and it’s still pouring. Being a parent myself, I think, “Now’s when it happens. Now is when the kid throws a tantrum in protest.”

But Christian is placid. His bellyache is gone or forgotten, and he’s skipping around in the parking lot and enlisting me as a straight man for his pranks. (I’m still a novelty, having just arrived to hike with him for three days.) “Knock knock,” he says.

“Who’s there?”

“Car go.”

“Car go who?”

“Car go beep beep.” He throws his head back and laughs, so the parking lot fills for a moment with bright peals of joy.

“How many miles can you hike in a day?” he asks me as we start hiking.

“I don’t know. About 20.”

“That’s nothing! I did 22 miles one day and I wasn’t even tired.”

• • •

How far is too far? How much toil and suffering should a kid take—and what for? A generation ago, back when children roamed the streets freely, pedaling their banana seat bikes in a time before helmets, no one fretted over such questions. When a six-year-old boy named Michael Cogswell thru-hiked the entire Appalachian Trail with his parents in 1980, there was nothing but feel-good rhetoric surrounding his hike. Newspapers made light of how the little boy crashed constantly, weighted by his pack, and this magazine ran a celebratory story in which the author, Michael’s stepdad Jeffrey Cogswell, waxed poetic about the trailside flora—“red trillium, violets, purple ironweed”—and lionized the little boy’s perseverance as a photo showed a wonderstruck Michael drinking from an ice-skimmed mountain creek.

Now, though, childrearing is a science, and sniping at other people’s parenting techniques may be our favorite contact sport. When journalist Lenore Skenazy decided in 2008 to let her nine-year-old son ride the New York subway alone, she received thousands of hate letters and was called “America’s Worst Mom.” (Her response: freerangekids.com.) Similar skepticism has surrounded two Texas sisters who run half-marathons. When The New York Times profiled Kaytlynn Welsch, 12, and Heather Welsch, 10, in 2012, the headline asked, “Too Fast Too Soon?” One reader responded, “This is child abuse.”

Any parent who loves the outdoors can find him- or herself pushing the envelope, sometimes unwittingly. I will confess that when my own daughter, now 20, was in preschool, I took her on a kayak trip during which our inflatable boat sprung a leak. Our tent and sleeping bags slipped out into the rapids and I spent a frigid, sleepless night chastising myself for being selfish and negligent. But that was just a weekend. To thru-hike the AT, Christian has had to climb over rocks and roots almost every day for nine months, overcoming challenges that defeat plenty of adults, even as his young sinew and bones are still growing. Naturally, his parents have critics. In one recent post on a Facebook page, a hiker named Yvonne called Andrea out. “If BB’s mother is still on here and viewing these posts, I want to challenge you!” she wrote. “I challenge you to take a moment, step back and ask yourself who this Appalachian Trail hike adventure and experience is all about... if it truly is about Buddy... allow him to explore, allow him stop and love the mountain views.”

An AT stalwart calling himself GreyWolf took a harder line, alleging that Dion and Andrea brought Buddy hiking in unsafe conditions. “The temperature never got above the 20s and was in the teens at night. Should I call social services?” he railed.

But the family’s Facebook pictures from Christian’s journey on the AT voice a strong rejoinder to skeptics. Here’s the boy standing atop Katahdin, his arms raised in triumph. Here he is catching snowflakes on his tongue on Christmas Eve in the Smokies. As I scroll through the images, I can’t help but marvel at how Christian has experienced so much delight at such a young age. And part of me wonders: Should we really be asking if Andrea Rego is a bad mom for setting her son on such an arduous task? Is the correct question, in fact, Is she the best mother ever?

• • •

Certainly, she started from a rough spot.

When Andrea got pregnant with Christian in 2008, she was in her second year of college at Stony Brook University, in New York. She was 20 years old, overweight, and ensconced in a nine-month romance with a man from whom she is now estranged.

“I hoped Christian would bring some stability to my life,” she says. The plan failed. After the birth, Andrea continued attending college for a year, but then quit to work full time. Logging 50 to 60 hours a week at the construction company, Andrea, who is 5’4”, ballooned to 200 pounds. “By the time I picked Christian up at daycare,” she says, “I was so tired that we just went to McDonald’s or ate frozen food in front of the television. Christian wouldn’t eat anything if it wasn’t in a package. He was addicted to TV.”

Soon, though, Andrea grew closer to her friend Dion Pagonis, who had his own unfulfilling (but lucrative) job on Long Island, working in a windowless room at Sherman Specialty, the world’s largest supplier of restaurant crayons. Dion, who is also 5’4”, once weighed well over 250 pounds. But he is not one to live in quiet desperation forever. He’s ambitious, in idiosyncratic ways. In high school, he earned his Eagle Scout badge supervising a team that re-created a Native American village. In college, at SUNY Fredonia, he was the president of Greek life.

In 2007, Dion bought a Wii Fit and began working out three hours a day. He lost 70 pounds. Not long after, Andrea joined a gym and began working out, too. By 2011, Dion was fit enough to try the AT, solo. (He made it 200 miles before twisting his ankle.) Later, he convinced Andrea to join him for a backpacking trip in Colorado. She had never before gone on an overnight hike, and she was still smoking a pack a day. Over a weekend, they covered only 7 miles. “It was very hard,” she says, “but I loved it—just being outside, away from Long Island.”

In spring 2012, finally, Dion engineered an escape plan. He and Andrea sold nearly all their possessions and moved west to Colorado, first to Boulder, then to Crested Butte, a ski town where Dion scored design gigs at elance.com and they operated a hostel called Butte Bunk. While Dion snowboarded, Christian (then four) and Andrea took to the bunny hill on skis. “By the end of the season,” Andrea writes at buddybackpacker.com, Christian “was blowing down moguls and double blacks on one of the hardest mountains in the United States. He has the endurance of an advanced athlete with a deep love for nature. Andrea and Dion have no choice but to live epic lives with him.”

The experience in Crested Butte changed the trajectory of their lives. Suddenly, the pair hoped to bring Buddy to California, so they could all learn to surf. They thought they’d like try a long-distance mountain bike odyssey somewhere. They wanted to put themselves on a path toward adventure, and test their own endurance as well as Christian’s. In Colorado, as the snow melted, Andrea envisioned another kind of adventure. “Why don’t we hike the Appalachian Trail?” she asked Dion in April of 2013. Crested Butte was about to button up for the off-season. So they bought the well-used Jeep for $1,500, loaded their gear, and headed east.

• • •

It’s very slow hiking with Dion and Christian, and also a little bit solemn. Both of them walk with iPods and headphones. Dion listens to rock, Christian to educational music and lessons—brainy stuff chosen by Dion. (The digital lessons are the backbone of Christian’s home-schooling program.) All I can hear, moving along through the woods, is the dull thud of footfalls and the rain pattering on the dead, sodden leaves. We roll along over gentle hills, passing rocky outcroppings that open onto the gray horizon, and eventually (inspired by his music, it seems) Christian begins skipping and weaving on the trail.

“Pay attention,” Dion tells him. “Look where you’re going.”

“I love the Octopus’s Garden song,” Christian says when it comes on his iPod.

In downtime at occasional hotels, Dion and Christian cuddle up together and watch movies on Andrea’s iPad. Out on the trail, though, the dialogue is nearly all safety-oriented during the 40 miles I hike with them. To me, Dion explains, “If he trips and breaks an arm, our hike is over.” In New Hampshire, Dion made Christian a promise: “If you don’t have any boo-boos when we get to Katahdin, I’ll give you some money.” Christian lost that challenge, scraping his knee in a crash.

Now, though, it’s Dion who’s holding us back. Still a bit chunky at 180 pounds, he isn’t a particularly fast hiker, and he’s plagued with what he calls “Fred Flintstone feet”-—his arches are almost convex. At times, Christian and I drift ahead. Then, I ask Christian about his audio lessons. He’s learning vocabulary words: nefarious, subvert, fetid, and encumbered.

“What’s the teacher saying right now?”

He squints a moment, listening. Then he parrots the saccharine voice from his iPod: “We’re so encumbered with red tape we can’t get any real work done.”

When we meet Andrea at a road crossing, Christian runs toward her, laughing, to hug her. We all get a moment of sweet reprieve, but only a moment. Andrea says, “I always feel like we’re a pit crew in a car race. It’s like, ‘You tie his shoes. I’ll put food in his mouth.’ We’re always rushing to get him back on the trail.” She turns to Christian. “Are you ready for some Pringles, Bud?” Looking back at me, she says, “He loves Pringles—that’s his favorite food.”

Christian takes a small stack, and then as we step into the woods, I glance back at our mission vehicle: The Jeep is a dull red, with “buddybackacker.com” and a big pair of angel wings, in yellow, that Dion drew on the hood. (The wings signify trail angels, as Andrea often gives other hikers rides.) The Jeep has 150,000 miles on it, but they’ve been hard miles; it looks like it might die on the next hill.

• • •

The Buddy Backpacker expedition is not a well-oiled machine, and by the time I joined, there’d been a medley of calamities. On the first night of the trip, after the family rolled out of Crested Butte, Andrea left her wallet at a convenience store. As Dion dislikes carrying money, the trio was broke. They made camp after midnight near Manhattan, Kansas, in a cold wind, and struggled setting up their tent for the first time. “I was shivering,” Dion remembers.

“After just two restless hours, the family pressed east, toward West Virginia and the start of their hike—and the start of their controversial trail strategies. Many hikers have attacked Andrea and Dion for being loosey-goosey—and also lazy—on the AT. Sometimes when faced with a big hill, they make things easy on themselves. They drove to the top of Mt. Washington twice, for instance, so Christian could hike down each side. (He never actually climbed Washington.) When it was snowing in the Smokies, they skipped ahead, down to Georgia, then came back weeks later. They took about 90 days off, in total, enabling Dion to earn much-needed money by doing design projects. They were simply hiking their own hike, to invoke the credo that pervades AT culture, but that counted little with backpacking’s grand poohbahs, who in many cases have built their lives around the AT and come to style themselves the keepers of the trail’s sacred mores.

“They were sloppy,” says Warren Doyle, a retired college professor who’s hiked the AT a record 16 times. “They did a lot of lollygagging, and they got into trouble because of that. They were out hiking far later into the winter than they needed to be.” (Doyle, ironically, has critics himself. On his Appalachian Trail Expeditions, a support vehicle carts gear for hikers, enabling them to sashay nearly all 2,000-plus miles bearing nothing but daypacks.)

Other critics questioned if they were actually on the trail at all, suggesting that Christian’s parents cheated by skipping several stretches of the AT, even as they pretend-logged the miles online.

“There are some people who are lying about thru-hiking the Appalachian Trail and, since it’s almost Christmas, I’m not going to name them yet,” wrote a man named Tom Bazemore on Facebook. “This will give them a chance to come clean and end their con game.” Bazemore, who runs a Georgia-based shuttle company, continued by directly addressing his targets: “You are certainly not the first to lie about hiking the entire trail but the fact that you are using a little child in this con is truly beyond belief!”

Seventy-one comments followed, most of them nasty, and Andrea snarled back: “I hope you all are completely ashamed of yourselves for spewing such nonsense. I can’t wait until we are finished and can laugh looking back at all you haters.”

I called Bazemore to ask which sections Buddy and his folks had skipped. His complaints zeroed in on a 30.3-mile stretch of trail between Newfound Gap, North Carolina, and Davenport Gap, Tennessee. “I shuttled some hikers there exactly when [Christian and Dion] were supposed to be there,” he said, “and I told these people to look for a man with a five-year-old boy. They never saw them.”

Dion had anticipated such critiques, however. In his own Facebook post, he wrote, “If I wasn’t hiking with Buddy, I would be skeptical of his accomplishment, too.” So along the length of the AT, he took photographs with a GPS camera and then posted them to a map at panaramio.com. His pictures are mostly of Christian standing at overlooks or streams, or by trees or on mountaintops, and they do not skip the section Bazemore questions. For those 30 miles, there are more than 20 photos, each one time-stamped. I scrutinized them one morning, and a story emerged of a small boy moving over rocky terrain, through ice and snow, at a little more than 1.5 miles an hour. There is little doubt that Buddy Backpacker progressed steadily northeast, toward Davenport Gap, in two long days, on December 1 and 2, 2013.

I called Bazemore back and asked him to point me toward other skipped sections. “Look,” he said, “I’m not going to go back and forth with you on this like we’re all in junior high school. I know what I know and I stand by it.”

• • •

The weather clears, and when we begin hiking on the second day, after camping, Christian is in high spirits. “Isn’t it beautiful out today?” he says. “The trail is nice and soft, and there are no roots, and it’s pretty flat right here. It’s even pretty warm.” He’s chatty now, and he speaks of seeing orange lizards on his AT odyssey, and turkeys, and red flying squirrels, and a rattlesnake, some wild ponies, and a moose. He doesn’t know the names of the plants around us. He’s experiencing nature as a small animal does, sensually, as a breeze on his back and a cold bite on his brow. Listening to him, I think of Michael Cogswell, the six-year-old thru hiker, now in his early 40s, who recently told me, “I wouldn’t trade my AT experience for the world. There’s a certain purity in doing something like that as a child. You can never get that back. But there are positives and negatives. By the time I was done with that hike, I wasn’t really a kid anymore. I’d walked so many miles. I’d carried my own clothes and a tent and helped wash the laundry at night. I’d had all this responsibility.”

Is Christian growing up too fast? He sure doesn’t seem world-weary, for he keeps begging me to tell him make-believe stories. I tell him one, finally. It’s about my plastic water bottle going “home,” to China. The water bottle has a hard-to-pronounce fake Chinese name that Christian loves repeating, his voice a high-pitched array of scratchy, whispery sounds. When the tale is done, he spends 30 minutes detailing the plot of the film Cloudy With a Chance of Meatballs. Then he asks, “Should I tell you about Cloudy with a Chance of Meatballs 2?”

Is he lonely—starved for attention from people besides his parents? Probably a little, but when I ask if he misses going to school, he isn’t entirely clear what school entails. Andrea says he enjoyed preschool on Long Island, but on the trail he only conjures up one memory. “They put me in with the babies,” he says with disdain.

I ask him if hiking ever gets boring. “That’s a silly question,” he says. “No!”

“Do you ever hate the AT?”

“Sometimes I don’t like it when it’s really hard. Then I just want to be done. I want Mommy to be right there in the middle of the woods and I just want to go to sleep right there.”

Later, I described my hike with Christian to Dr. W. Douglas B. Hiller, an orthopedic surgeon at North Hawaii Community Hospital and a one-time chief medical officer for the triathlon at the Olympics. He said, “I doubt they caused him any physical harm. As long as it was a happy family hike and he wasn’t being pushed, or made to keep going when he was limping, he should be fine. If he got some bruises and cuts, well, that’s what little kids do all day long—they run around and jump and fall and get up.”

I searched at length for a child psychologist who might object to Hiller’s sanguine take. I couldn’t find one, and I decided that the hubbub over Andrea’s parenting was rooted partly in fear: Andrea is different than most AT hikers. She’s from working class Long Island. She’s combative at times. Yes, she and Dion brought Christian hiking on a very cold day. But what’s the harm in dressing warmly and hitting the trail? Yes, Dion sometimes carps at the kid. As do many parents who steer their children toward more culturally accepted goals—piano, soccer, spelling bees. Why should hiking be any different? In fact, it’s easy to see the experience in a very different light. Christian and his family are hiking America’s most beloved and fought-over trail in pursuit of happiness, and they’re happy most of the time. Together, they’ve found a way to engage with the world—to commune with its beauty and have an adventure. This is what matters.

On the last day I’m on the AT, Andrea picks us up at dusk, to drive us to the nearest shelter, where we’ll camp. It’s cold outside, so we savor the warm blast of the car’s heater. When we park, Dion limps down the short path to the shelter. Christian leaps over the puddles. Andrea cooks us all dinner. Then the next morning, backing out, she runs over the gas stove. Under her breath, she says, “Shit!” Then she laughs and throws the stove into the Jeep and drives on.

• • •

I see them only one more time, eight months later, on a rainy afternoon last September in the small town of Trout Lake, Washington, as they take a break near the end of their Pacific Crest Trail thru-hike. Trout Lake is a forested Nowheresville, and after 11 straight days on the trail they’re ensconced in drab tasks—laundry, email, cleaning out their packs. Still, as I pull up to the Trout Lake Grocery to find Andrea standing there on the porch, with Christian entwined in her arms, she exudes a certain glow. There’s an ease about her, a softness to her skin. She’s happy—you can tell that without even asking questions. And she’s sunbaked and lean now, 35 pounds lighter than when I’d last seen her. She’s been hiking the whole way this time, with both her and Dion carrying packs. The Jeep is long gone.

“We did 23 miles yesterday before four o’clock,” she says, looking down. “Didn’t we, Buddy?”

“Yeah,” Christian says, rocking a bit in his mother’s arms. He’s sleepy-eyed and determined, it seems, not to take the bait. “Actually,” he says, “it was 22.8.”

“What’s been your favorite part of the PCT so far?” I ask.

“Whitney,” he says. “It was cool. We were way up there. It felt like the end of the trail.” There’s still a kid’s wonder in his voice, but it’s more contained now. He’s 2 or 3 inches taller, and there is, suddenly, a grace about his small, lanky person. It seems almost certain that in a few years girls will go crazy for him and that he’ll deflect their ardor with a languid ease.

“And what else was fun?” I ask, digging a little more.

“Goat Rocks,” he says, referring to a nearby boulder field that stretches on for a couple miles. “I like doing hard stuff. And this house,” he says, meaning the store, where they’re staying in an upstairs motel room. “At night, they light up these lights on the porch and it’s beautiful. It looks like Christmas.”

When Dion emerges, fresh from a shower, I see he’s lost weight as well. He’s more than 30 pounds lighter and also ebullient, almost jolly. The tenseness I’d seen before on the AT, as he tried to corral a restless kid and negotiate complex car logistics, has vanished. This time, the three of them have all hiked together. There is, it seems, a new calm in Dion’s muscles. “This trail is easier than the AT,” he says. “It’s well-maintained, it’s graded. It’s not rocky and you can actually get a good stride going.”

We walk across the street to get lunch, and Andrea and Dion update me some. Christian, they say, now likes to wield his bamboo hiking poles like Ninja swords. They’ve landed a host of sponsors—a tent sponsor, a pack sponsor, even a socks sponsor—and at one point, resting from the trail, they encountered a lovely 18-year-old girl who spent the afternoon teaching Christian how to twirl a hula hoop.

“You liked that didn’t you, Bud?” Andrea asks.

“Yeah,” he says, looking down at his fries. “That was good.”

What jumps out is how steady they all seem. They’re no longer the hapless outsiders of the backpacking world. No one is savaging them on Facebook anymore, and their goal of completing the Triple Crown in 2015 no longer seems outlandish. Barring catastrophe, they will get the job done. Then they’ll move on to surfing or mountain biking or whatever. Everything will work out for Christian, more or less; he’ll clearly be okay.

But to Christian, the unlikely peace that his family enjoys wandering the world is old news. He doesn’t want to sit there and talk about it. There’s a trampoline behind the store, and he keeps looking out the window toward it. Eventually, Andrea lets him go. He runs over to it, loose-limbed, his body lit with delight. He climbs inside the trampoline’s protective black mesh fence, and begins jumping, giddy and laughing as he sails into the sky.

Bill Donahue has written for The Atlantic and The New York Times Magazine. With his daughter, he recently swam between remote Caribbean islands, and lived to tell the tale.